


The Waiter and the Businessman

by followyourenergy



Category: Supernatural
Genre: Businessman Dean Winchester, Christmas Eve, Christmas Fluff, Diners, First Christmas, Happy Ending, Homelessness, Light Angst, Lonely Dean, M/M, SPN Holiday Mixtape, Soup Kitchens, Waiter Castiel, hopeful
Language: English
Status: Completed
Published: 2017-12-19
Updated: 2017-12-19
Packaged: 2019-02-17 03:00:58
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,844
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13067724
Author URL: https://archiveofourown.org/users/followyourenergy/pseuds/followyourenergy
Summary: Dean Winchester, CEO, frequents the diner on the corner of Main and South for lots of reasons: pie, the jukebox that plays 80s music, and Castiel, the sweet, handsome waiter who always has time for Dean. When he sees Castiel unexpectedly on Christmas Day, he learns more about the quiet man... and receives two precious gifts that money could never buy.





	The Waiter and the Businessman

**Author's Note:**

> Wishing you a beautiful holiday season! <3

Several nights a week, Dean stops into the little diner on the corner of Main and South. He enjoys their pie. He enjoys the old jukebox that plays the best of the 80s and still only costs fifty cents per play. Mostly, though, he enjoys Castiel, the attractive dark-haired waiter who is working every night Dean drops in. He doesn’t always have time to hang out and talk, but he always has a ready smile and seems genuinely interested in Dean’s day when he asks… and he always asks.

Colorful lights hang around the perimeter of the large, open space, and a Christmas tree glitters with tinsel in the corner. The diner is busier than usual tonight, or maybe that’s because Dean’s in a little earlier than usual. It’s Christmas Eve, and there are families grabbing quarts of the diner’s homemade coleslaw or one of its delicious homemade pies to bring to family gatherings. A few people are eating a light supper and chatting amiably about the next day. There’s a large group of twenty-somethings at a set of three tables pushed together, and a man sitting in a corner by himself, reading a newspaper. Castiel greets him by name and invites him to sit wherever he likes. Dean sits at the end of the counter. He likes sitting there so he can see Castiel bustling around the restaurant and be near the man when he comes around to enter money into the register. He’s pleasant company, even in his quiet busyness.

“Great,” Castiel mutters under his breath sarcastically as a group of men enter the diner, loud and arrogant. It catches Dean by surprise. He doesn’t think he’s ever heard Castiel say anything negative about anyone. They take a table in the middle, where no one can miss them. Castiel’s co-worker stands nearby, watching them sit and fumbling with her pen as she chews on her lip. Dean is pretty sure it’s her section. Castiel eyes the group of obnoxious men warily before turning to Dean at the counter. “Dean, Nora will be taking care of you tonight. Nora, switch with me.” She hurries over and gives a small, grateful smile to Castiel. “Dean likes his pie warmed, with a scoop of vanilla ice cream on the side. He says he likes his coffee black but he actually likes it with two sugars.” He smiles shyly at Dean and grabs his notepad, digging a pen out of his apron and heading for the large table. Dean rubs his neck and smiles down at the countertop before acknowledging that yes, she can leave him with a couple of sugar packets and yes, he will take some ice cream with that blueberry crumble pie, but he’s going to have dinner first. He orders a turkey dinner with mashed potatoes and corn and extra gravy and cranberry sauce. Nora is sweet and takes his order quickly and efficiently.

Dean watches and listens as Castiel takes the orders of everyone in the large party and serves them. They keep him busy, asking for refills and appetizers and rolls and extra napkins, though they seem to have plenty on the table. They’re a demanding bunch; Castiel is really earning his tip tonight. Dean imagines dumping Castiel’s pitcher of water all over them just for fun.

Dean is distracted for a while when a few folks from town recognize him and come to chat with him and wish him a Merry Christmas, and he ends up staying longer than he meant to stay. The restaurant is mostly empty now, except for Dean, the elderly man with the newspaper in the corner, and the assholes in the center of the room. Nora locks the doors and begins to clean up. She refreshes Dean’s coffee and presents him with the pie. The temperature is just right and the ice cream is melted just enough to create a sweet, creamy puddle in which to swirl forkfuls of the blueberries while still maintaining a decent lump of the sweet stuff to scoop into his mouth whole with the final bite. Castiel must’ve made it; no one else gets it right the way he does. He orders an extra slice to go for tomorrow and settles his bill, leaving a large tip for Nora.

Castiel brings a to-go box to the elderly man; by the smell of it as he breezes by, it contains the same turkey meal that Dean ate. Dean watches the man stand and pat Castiel on the arm as he utters something slowly and with much effort. Castiel responds with something Dean can’t hear but he knows is kind, just because it’s Castiel.

“Will you be alright for a moment, Nora?” he asks, his eyes darting to the large party and then to Dean. His eyes are hard when they flit onto the loudmouths but soften when they rest on Dean, a question lingering in their depths. She nods, and Dean does the same, a silent agreement to keep an eye on things while Castiel is gone. He’s humbled by the trust the handsome waiter places in him. Castiel supports the elderly gentleman with his arm and walks him out, returning a few minutes later.

It seems the rowdy group waited for Castiel to return to settle up their bill, and when they do they are rude and critical as they flash their wads of cash in their money clips. Castiel takes it in stride, not warm and friendly like he is with Dean but not giving them a taste of their own medicine, either. They finally leave and Castiel locks the door behind them. The air seems to lighten immediately, and Dean says, “Well, they’re a bunch of assholes, aren’t they?”

“Yes,” Castiel says simply, looking up briefly and sharing a private smile with Dean before counting the register.

“Did they stiff you, Cas?” Nora asks as she scans the messy table. He shrugs and continues counting. “Oh, no, I’m so sorry! I should’ve taken the table. They just creeped me out and…”

“Nora, it’s fine.”

“Well, let me give you the tip from the other large table then…”

“Keep it, Nora.”

“It was your table originally…”

“Nora,” he says gently as he straightens up from his position over the register, “keep it. You have a baby at home. That baby needs things. I’m fine. I have what I need.” Nora gives in and pulls Castiel into a hug, whispering her tear-soaked thanks into his shirt.

Dean, entranced by the tender act of generosity before him, is startled by a woman with a larger-than-life presence entering from the kitchen. “Hey, hey, no cryin’ on Christmas Eve!” she chides gently. They smile at the older woman as she says, “Alright, so I know you’re dyin’ to get out of here, but we gotta do our question first. It’s tradition.” She turns to pick up a box of conversation starter cards near Dean and notices him. “Well, who are you and what are you doin’ in my restaurant after closin’, young man?”

“That’s Dean,” Castiel answers for him, “and he’s a regular.”

“That doesn’t explain why he’s still here.” She eyes him with an assessing stare, leaning on an elbow. Dean shrinks back as if he’s being scolded.

“We were chatting, Missouri. He’s one of your best customers and he’s a good guy, so don’t scare him off,” he teases, then adds, “Dean loves your pies.”

“Well, he ought to. Freshly made. He has good taste.”

“I love everything about your restaurant, ma’am,” Dean says as he finds his voice. “The food, the atmosphere… the staff.” He glances at Castiel, who blushes and straightens out the salt and pepper shakers on the counter.

Missouri scrutinizes him again as her eyes dart between the men and says, “Yes, you have good taste, Dean. Now, since you’re here, you have to answer the question, too.” While Missouri passes her hand over the large deck of cards, feeling for the “right” card, Castiel explains to Dean that they answer one question in the morning and another every night so that the staff get to know each other better because she thinks it helps with staff retention and morale. She pulls out a card and reads out, “What would you do with a million dollars?”

Nora answers right away. “I’d buy a house and go back to school, or maybe stay home with my daughter until she starts school.”

“Those years are important, dear. Oh, when my babies were little we had the best time,” Missouri reminisces. “I’d renovate the diner and put money away for my retirement.”

“You’re never going to retire, Missouri,” Castiel jokes gently.

“Probably not,” she admits. “How about you, Dean?”

Dean hesitates. He has millions of dollars to his name already as the CEO of a successful corporation with branches around the world. “Uh… well, I guess I’d just invest it and make more. For a rainy day or something.”

“Smart man,” Missouri nods.

“And you, Cas?” Nora asks.

He smiles wistfully as he takes a deep breath. “I’d put half of it in some safe investments for my daughter’s college fund, fly out to visit her, pay off my own college loans and medical bills, donate some to charity, and if there was any left I would… upgrade my current living situation.” Missouri gives him a loving smile and grasps his hand. Dean tries to hide his shock at the fact that Castiel has a daughter. He sees no ring on his finger, though, so he’s still a bit hopeful that maybe the man is single and available.

“Well, looks like we’d all be smart with our money. Not a wasteful one among us!” Missouri exclaims. “Well, go on, get out of here and have a Merry Christmas.”

The co-workers exchange hugs. Missouri whispers something in Castiel’s ear and he shakes his head but squeezes her tighter. When they crowd at the door, Dean takes this as his cue to walk out with them. He’s hoping to walk out to Castiel’s car with him and maybe talk with him some more, and maybe by some Christmas miracle he’ll get up the nerve to ask the guy out. But Castiel doesn’t walk out with them; he says he has a couple of things to wrap up and he’ll lock up everything. He wishes them all a Merry Christmas and tells them he’ll see them on the 26th.

“Merry Christmas, Dean,” Castiel says. He squeezes Dean’s shoulder gently through his thick wool coat, and it warms Dean more than the coat ever could.

“Merry Christmas, Cas,” Dean says. “Hey, you gonna be long?”

“I’m going to be a while, yes,” Castiel answers, darting his eyes away briefly before returning his gaze to Dean. “I’ll see you soon, I hope.”

“Yeah, Cas. Soon,” he agrees. Impulsively, he gathers the dark-haired man in his arms. He’s stiff at first, but soon relaxes and returns the embrace. Dean pats him on the back as they separate. “Night, Cas.”

“Good night, Dean,” Cas replies with the same shy smile he gave Dean earlier that night. Dean wonders if it means his gut is flip-flopping the same way Dean’s is.

Dean waits anyway, even though Castiel said he’d be a while. He watches Castiel putter around for a few minutes before he turns the lights off. Dean waits some more, assuming Castiel will be coming out the door any minute, but he doesn’t. Dean drives around to the back, looking for his car. There are no cars there. He reasons that Castiel must’ve left out the back way and Dean never saw him, but it doesn’t sit quite right with him. He sighs and goes home to his exorbitant, empty house.

Dean’s in no particular hurry in the morning, since he has nowhere to go until 11:00. He makes himself some high-octane coffee (as his assistant Becky calls it) and shuffles out to his living room to catch up on some paperwork. He looks around the room as his computer boots up; it’s bland and decidedly unfestive. He doesn’t even have a tree. It’s no big deal, though, he decides, since he doesn’t have anyone to spend Christmas with, anyway. His mother is dead, his father is an off-the-rails drunk who’s MIA half the time, and he’s estranged from his brother since their huge fight about their father a few years ago. He probably could have visited Bobby, but he has Ellen and Jo now and he doesn’t want to intrude. He shakes off the thoughts of his family and absorbs himself in his work. Before he knows it, it’s time to shower and head out.

The soup kitchen next to the church is busy today, full of people who wouldn’t otherwise have a hot meal at Christmas (or maybe any other day). Soup kitchens and homeless shelters have a special place in his heart, since he spent a lot of time in them as a kid during the times when his father had been unable to keep a job. He usually donates money to them, but today he figured he’d donate his time so someone else could be home with their family. The volunteers are nice. Many of them are a little rough around the edges, but their hearts are made of smooth, gleaming gold. They give him a hair net and a pair of plastic gloves and they don’t give a shit how much money he has or how pretty he is. They point him to pans of mashed potatoes and stuffing and tell him to get to work. It makes him grin.

The people come one after the other, and Dean tries to give each of them a bright smile and a cheerful greeting. The faces blend after a while, until one face stands out… the one that always stands out to him.

“Cas?”

Castiel, who had been talking soothingly to the bedraggled man next to him, stops and blinks. “Um, hello, Dean. Merry Christmas.”

“Merry Christmas,” Dean replies automatically, his confusion etched onto his face. “What… what are you doing here?”

“Same as everyone else, I imagine,” he mutters, looking pointedly at his tray. He shifts on his feet and won’t make eye contact.

“But… I don’t… I don’t understand. Why are you _here_?”

“I’m holding up the line. Excuse me.” Castiel picks up his scarcely-filled tray abruptly and leaves the line, disappearing into the crowd.

“Shit, fuck,” Dean mutters to himself. His smile disappears and he looks around frantically for Castiel. He finds him sitting at a table with several people; a little boy seems fascinated by him and is talking his ear off. He swivels his head around to see if he can find someone to take over his job so he can talk to him and apologize, but everyone is too busy. He keeps his eyes fixed on Castiel as he absently plops scoops of potatoes and stuffing onto trays; he’s paranoid that if he takes his eyes off the man, he will leave.

The line finally dies down and Dean cleans up the area. Castiel is still sitting at the table; he’s having some sort of staring contest with the boy. Dean is irrationally jealous of the little boy who gets to have Castiel’s undivided attention. The boy must blink, because Castiel raises his hands in victory and then they hunch down to start again. The butterflies that always seem to inhabit his gut when Castiel is around now feel like they’re weighed down with concrete shoes, a strange heaviness accompanying the usual fluttering. Dean bites his lip as he gathers the nearly empty metal basins of food and carries them into the kitchen. He thinks about everything he wants to say to Cas as he empties the remaining food into smaller containers and brings the empty pans to the sink, where several people are rinsing, washing, and drying. His job done, he whips off the apron and rushes out to explain himself to Castiel… who isn’t there.

“Damn it!” he curses through clenched teeth. He rubs his burning eyes with the heels of his hands. “Can’t do anything right, fuck.” He scans the room but there’s no trace of the gentle soul who’s managed to break through Dean’s defenses with his tiny smile and his sincere attention and his kind, generous heart. Seeing the family he sat with gathering their things, he strides quickly over to them. “Hi, I’m sorry, but do you know where Cas went? The guy who was sitting with you?”

“He mentioned the church next door,” one of the women says, and her -- friend? partner? -- confirms this and adds, “He said he was going to light some candles.”

“Thank you,” he calls over his shoulder.

The church is cool and empty save for Castiel, who sits quietly near the front. Evergreen garlands with twinkling lights drape the walls and poinsettias grace the altar. A few votive candles burn in ruby red candleholders. Dean stands next to Cas’ pew, one hand stuck in his pocket and the other tapping nervously on the end of the long bench. “I’m sorry, Cas,” he blurts, his voice too loud in the sacred quiet. “I was insensitive, I was just surprised…”

Castiel looks up at Dean and stills his hand by placing his on top. “Dean. Sit.”

Dean sits.

“Most of us are just one event away from homelessness,” Cas starts. “One job loss, one breakup, one accident, or in my case, one long illness.” He stares at the candles and Dean watches the flames sway in Castiel’s startling blue eyes. “I had pancreatitis. I was hospitalized for a long time. I lost my job, lost my house, lost my partner and daughter because she couldn’t handle the stress. She met someone and when her new partner got stationed in Germany, they moved with him. That was two years ago. I kept an apartment for a little while with what savings I had left, but it got to be too much and I couldn’t afford to pay my other bills and Claire’s child support. By then I’d recovered enough to get a job, but people just weren’t hiring graphic designers, I guess. So I took the job at Missouri’s, and she let me stay in a little room in the back that everyone else thinks is some private storage room of hers. Which it is, but only I have a key. No one else knows I stay there. I work pretty much every day. She can’t afford to pay me much, but I get meals on the days I work and I have an arrangement with the shelter to let me shower a few days a week. She offered to let me live with her, but she has one of her kids and a couple of grandkids in a little trailer and I just thought it would be too much.”

Dean feels his throat tighten as tears threaten to spill down his cheeks. “Fuck, Cas. I’m so sorry.”

“It’s alright, Dean.”

“No, really, I…”

“I know, Dean.” He takes Dean’s hand and presses it between his two slightly chilled ones. “I’m not telling you all this to make you feel bad.”

“What about your family, Cas? Why aren’t they helping you?”

“I’m an only child, and my parents live across the country. I moved out here to Chicago for college because I wanted to get away from the repressive nature of my community and… well, here I’ve stayed. They don’t know I’m homeless. If they did, they would just worry and pester me to come home, and they don’t really understand what it was like to grow up bisexual in that community. It was... not welcoming, shall we say.”

A shiver of hope races through Dean at Cas’ disclosure of his bisexuality, but he pushes it aside for his greater concern. “Wow, yeah, I get that. It sucks. But I mean, could your folks help you financially?”

“They think I’m working. My parents, aunts and uncles, cousins -- they’re all working-class people who work hard for every cent they earn, so I will not ask anything of them.”

Dean scrunches his brows in thought as he looks down at his hand, still encased in Cas’ cool, dry ones. “Wow, Cas. All this shit, it’s gotta be depressing.”

“Believe it or not, Dean,” Cas says as he links their fingers and presses their palms together, “I’m not unhappy. Certainly, life could be easier. I’m still looking for work in my field and eventually I would love a home of my own again, and things are positively arid in the romance department.” He gives Dean a small, sideways grin that Dean returns. “But I’m living my life. I have friends, I’m not sleeping in the cold, I volunteer at the shelter, I use the diner’s wi-fi to talk to Claire and my family on Skype. I’m healthy. I’m building my savings with what I have left over at the end of the month. I have it so much easier than so many others.”

Realization dawns on Dean. “You knew those jerks were going to stiff you last night.”

“They do it to everyone,” Cas says with a shrug.

“But you took the table so Nora wouldn’t lose out on a tip. You gave her the customers you knew would tip well.”

“She has a baby she’s raising by herself. She needs it. She shouldn’t be the victim of a bunch of selfish assholes.” Cas smirks and Dean smirks with him. The epithet is fitting but sounds strange, either because it’s Cas saying it or because he’s saying it in a church, and Dean finds himself giggling like a schoolboy.

“And I bet you bought that old guy’s supper, too,” Dean guesses.

“He doesn’t have anyone else. His family is far away, too, and his wife died last year. I just wanted to make sure he had something special for today.”

“Cas… damn,” Dean shakes his head and wipes his eyes with his free hand.

“Dean,” he says, rubbing Dean’s hand. “Dean. Like I said before, I didn’t tell you about my life to make you feel sorry for me. I just… I just wanted to tell you, I guess. And I want you to know that you can find happiness, too.” He smiles a bit to himself and turns to Dean.

“The million dollar question was the wrong question for you,” Cas remarks. “The better question for you would’ve been, ‘What would you do if you had a million hours?’ Time just for you, to do whatever you wanted to do. What would you do, Dean?”

Dean answers immediately, a dreamy glaze settling over his eyes. “Take a drive. A long one. See all the people, places and things I can. Camp under the stars. Eat pie in every state. Take pictures.”

“Funny how working ninety hours a week and amassing all the money you can didn’t make your list of activities.” Dean twists his lips into a wan smile. “Millions of dollars won’t necessarily make you happy, Dean. But I guess you know that, hmm?”

Dean meets his eyes in surprise. “You know…?”

“That you’re rolling in cash? Yes,” he says with a laugh. “One of the waitstaff told me, a few weeks ago. She recognized you from the newspaper, I guess.”

“Ah,” Dean puffs, then asks, “Wait, what makes you think I’m unhappy?”

“Just a feeling. You come into the diner a lot, so I assume you’re looking for companionship. You don’t come in with anyone else and you don’t talk about a significant other. You talk about a brother but it’s all in the past, nothing recent. You’re talking to a homeless guy in a cold church on Christmas Day, and you haven’t kicked the guy’s ass for holding your hand.” He huffs a self-deprecating laugh and Dean gently jabs him in the shoulder. “And, I don’t know, your answer to the million dollar question seemed to lack any enthusiasm.”

“Yeah, well, you’re right, I guess. I mean, I have all this money but it doesn’t do shit to keep me warm at night, you know?”

“Well, I suppose you could use it as a blanket or something.” Cas winks and Dean rolls his eyes with a smile.

“Money provides a lot of things, but it doesn’t give you friends and it doesn’t fix relationships.”

“You’re right, it doesn’t. But you’re a very likable man, Dean, and I find that most things aren’t fixed by money, but by compassion and an attempt to understand each other. Friendships and other relationships thrive on both.”

Dean nods sadly. “Yeah, you’re right. My brother… we had a bad fight a long time ago, and we’ve never fixed it.”

“So fix it, Dean. Can it be fixed?”

“I don’t know.”

Castiel rubs Dean’s knuckles. “What better day to find out than Christmas Day?”

Dean exhales slowly, considering Cas’ words. He is unhappy, and he misses his brother. He has nothing to lose and much to gain. He digs his phone out of his pocket and unlocks it, then scrolls to Sam’s name. “Here’s hoping his number is the same,” Dean jokes weakly. Cas flashes him a reassuring smile.

The phone rings once, twice, three times before a voice he hasn’t heard in years answers the phone breathlessly. “Dean? Dean, is that you? Are you okay?”

The tears he’d just barely held back before fall freely now as he says Sam’s name over and over. He reassures his brother that he’s fine. Cas pumps his hand once and walks away to give Dean space; he kneels before the jewel-toned votives and bows his head. Dean is grateful for Cas’ thoughtfulness. He speaks to his brother quietly, the old tensions melting like the snowflakes meeting the tire-warmed street just outside the carved wooden doors. There’s a lot to work out, but compassion and an attempt to understand each other fixes a lot, he’s heard.

“Everything okay?” Cas asks when Dean kneels next to him. For a moment Dean doesn’t answer, instead bowing his head and saying a silent thank you for second chances and new beginnings.

“Yeah,” Dean says finally. He inserts money into the donation box and lights a candle for his mother, then steps back and watches the flame dance like she used to in their kitchen, Dean balancing on her feet. Castiel stands and brushes his knees, straightening the worn denim.

“I’m glad.” Castiel turns and stretches his arm out to snag his jacket on a finger, then shrugs into it. Dean buttons his coat to the top and wraps his red cashmere scarf around his neck. He peeks at Cas’ coat out of the corner of his eye. It looks too thin for Chicago winters, but he says nothing. They wander outside. There are people milling around, people that are probably waiting for the shelter to open for the evening. Despite the cold and the fact they don’t have a home to call their own, most are smiling, filled with good food and a childlike pleasure at having snow on Christmas (even if it’s quite unwelcome at other times of the year). A few of them wave at Castiel, and he waves back. They walk until they arrive at Dean’s car, where they alternate between staring at each other and at their own feet.

“I’m sorry for my reaction back at the soup kitchen,” Castiel says suddenly. “I… I’m not ashamed of being homeless, exactly, but I… I really didn’t want you to know.”

“Why not?” Dean asks, low and tender.

Castiel smiles and looks away. “People look at you differently when they know. I… I had hoped that at some point I’d be able to… when I had a better job and an apartment, I mean… I’d hoped to, um, take you… out.”

A cold breeze kicks up, its icy fingers tousling Castiel’s hair, but it’s Cas’ words that have Dean shivering. Did he really mean…?

“Out? Like a date?”

“Yes. If I… read the signals correctly…” Castiel stammers, fingers clenching with nerves.

“Cas,” Dean says, grasping Cas’ arms, “please don’t make me wait. I’ve waited months. Besides, money doesn’t buy happiness, right? I’d be happy just taking a walk with you, or skating on a pond, or…”

“Dean,” Castiel says as he takes Dean’s face in his chilly, ungloved hands, “will you spend Christmas with me? I have a tiny fake tree and leftover meatloaf and a copy of _Elf_ I borrowed from Missouri.”

Dean pulls Castiel’s hands into his and rests their foreheads together. “I’d love to,” he says.

And so they do. And the next Christmas they serve lunch at the soup kitchen, Sam by their side, then go home and introduce him to their traditional Christmas meatloaf in their fully-decorated house. And after Sam falls asleep, they put _Elf_ in the Blu-ray player and ignore it completely while they make out… another Christmas tradition they hope to keep going for many years to come.


End file.
